EP0618271B1 - Composition de caoutchouc de silicone - Google Patents

Composition de caoutchouc de silicone Download PDF

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Publication number
EP0618271B1
EP0618271B1 EP94105172A EP94105172A EP0618271B1 EP 0618271 B1 EP0618271 B1 EP 0618271B1 EP 94105172 A EP94105172 A EP 94105172A EP 94105172 A EP94105172 A EP 94105172A EP 0618271 B1 EP0618271 B1 EP 0618271B1
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Prior art keywords
parts
weight
component
silicone rubber
groups
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EP94105172A
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German (de)
English (en)
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EP0618271A3 (fr
EP0618271A2 (fr
Inventor
Hideki Main Office For R. & D. Kobayashi
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DuPont Toray Specialty Materials KK
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Dow Corning Toray Silicone Co Ltd
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B28/00—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements
    • C04B28/02—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements containing hydraulic cements other than calcium sulfates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences

Definitions

  • This invention relates to a silicone rubber composition that can be used to make a silicone rubber having good processability, good molding characteristics, and good physical after curing.
  • silicone rubber compositions can be used to make molded products having good resistance to both heat and cold, these compositions are used for applications requiring the above-mentioned properties.
  • silicone rubber compositions containing fluorine resin powders were introduced by patent applications.
  • a conductive silicone rubber having an improved rolling processability and containing fluorine resin powder in the organopolysiloxane raw rubber is disclosed in JP-A 58-194949.
  • a rubber-type elastic material used for typing characters and having both good abrasion resistance and good dimensional stability, and containing fluorine resin powders such as polytetrafluoroethylene, in the silicone raw rubber is disclosed in JP-A 60-36171.
  • fluorine resin powder when a large amount of fluorine resin powder is used, the viscosity of the silicone rubber composition becomes so high that both the processability and the molding properties are decreased.
  • this invention provides silicone rubber compositions with excellent physical properties after curing, as well as with good molding properties and processability. It is prepared by mixing fluorine resin powders and specific organopolysiloxane into a silicone composition containing vinyl functional diorganopolysiloxane and reinforcing silica.
  • This invention therefore introduces a silicone rubber composition, comprising (A) a diorganopolysiloxane containing vinyl groups (100 parts by weight), (B) a fluorine resin powder (0.01-50 parts by weight), (C) an organopolysiloxane (0.01-40 parts by weight) containing a unit of the following formula: F(CF 2 ) a CH 2 CH 2 Si(Me) n O (3-n)/2 wherein a is an integer of 4 or greater, n is 0 or 1 or 2, and Me denotes a methyl group, (D) a reinforcing silica powder (10-100 parts by weight) having a specific surface area of at least 50 m 2 /g, and (E) a curing agent.
  • A a diorganopolysiloxane containing vinyl groups (100 parts by weight)
  • B a fluorine resin powder (0.01-50 parts by weight)
  • C an organopolysiloxane (0.01-40 parts by weight
  • the organopolysiloxane containing vinyl groups as component (A) of this invention can be any conventional organopolysiloxane used as the chief component of a silicone rubber.
  • examples include the following: dimethylpolysiloxane with terminal dimethylvinylsiloxy groups; copolymers of a dimethylsiloxane and methylvinylsiloxane, having terminal dimethylvinylsiloxy groups; copolymers of a dimethylsiloxane and methylvinylsiloxane having terminal trimethylsiloxy groups and methylvinylsiloxane; and copolymers of a dimethylsiloxane and dimethylvinylsiloxane having terminal dimethylhydroxysiloxy groups.
  • the preferred content of the methylvinylsiloxane units are 0.1-5 mol%.
  • the polymerization degree of this component is 100-20,000.
  • fluorine resin powder used as component (B) for the composition of this invention examples include polymers of polytetrafluoroethylene or copolymers of tetrafluoroethylene and other monomers.
  • examples of other monomers include: hexafluoropropylene, chlorotrifluoroethylene, perfluoroalkyl vinyl ether, perfluoroalkoxyalkyl vinyl ether, trifluoroethylene, perfluoroalkylethylene.
  • Either spherical, oval, flaky, cylindrical, stringy or fibrous primary particles of this component can be used.
  • the size is suitably 100 ⁇ m or less, preferably 0.05-10 ⁇ m.
  • the amount of this component is 0.01-50 parts by weight per 100 parts by weight of the component (A), preferably 0.1-20 parts by weight per 100 parts of (A).
  • An organopolysiloxane containing units of the formula F(CF 2 ) a CH 2 CH 2 SiMe n O (3-n)/2 is used as component (C) for this invention.
  • This component characterizes the composition of this invention, and works as a compatibilizing agent for components (A) and (B).
  • a is an integer of 4 or greater, e.g., 4 or 6 or 8. However, these can be mixed.
  • the variable n is 0 or 1 or 2. When n is 0 or 1, the units of F(CF 2 ) a CH 2 CH 2 SiMe n O (3-n)/2 are located in the main chain of this component.
  • n 2
  • the units of F(CF 2 ) a CH 2 CH 2 SiMe n O 3-n/2 are located at a terminus of this component. Either a straight-chain, branched, or ring structure may be suitable for this component.
  • the viscosity of this component is preferably in the range of 10-10,000 mPa.s (cP) at 25°C.
  • the amount of this component to be used is from 0.01-40 parts by weight per 100 parts by weight of component (A), preferably 0.1-10 parts by weight. When used at level of less than 0.01 part by weight, it is not effective as a compatibilizing agent for components (A) and (B). At more than 40 parts by weight of (C), the physical properties of the silicone rubber deteriorate as the composition is cured.
  • organopolysiloxanes of the following formulas: F(CF 2 ) a C 2 H 4 Si(Me) 2 O(Me 2 SiO) x Si(Me) 2 C 2 H 4 (CF 2 ) a F (a) Me 3 SiO(F(CF 2 ) a C 2 H 4 SiMeO) y (Me 2 SiO) z SiMe 3 (b) and
  • the variable a of formula (a) is the same as mentioned above.
  • the variable x is an integer from 0-300. When x is more than 300, this component is not effective as a compatibilizing agent.
  • Examples of synthesis methods for the preparation of organosiloxanes of formula (a) include the following: hydrolysis of fluoroalkyldimethylchlorosilane, cohydrolysis of both fluoroalkyldimethylchlorosilane and dimethyldichlorosilane, and equilibrium polymerization of fluoroalkylmethylpolysiloxanes made by the above-mentioned method and cyclic dimethyl polysiloxanes in the presence of a polymerizing catalyst.
  • variable a of formula (b) is the same as mentioned above; y and z are integers of 1 or greater.
  • the ratio y / z is from 0.1 to 0.9 and ( y + z ) is from 2 to 1,000.
  • ( y + z ) is more than 1000, the viscosity of this component becomes so high that the effectiveness of this component as a compatibilizing agent is decreased.
  • the organopolysiloxane of formula (b) is a copolymer, examples including both random copolymers and block copolymers.
  • Synthesis methods for the preparation of organopolysiloxanes of formula (b) include the following: cohydrolysis of a fluoroalkylmethyldichlorosilane and dimethyldichlorosilane, followed by equilibrium copolymerization with a disiloxane of the formula (Me 3 Si) 2 O in the presence of a basic catalyst; conventional dehydration polycondensation of ⁇ , ⁇ -dihydroxypolyfluoroalkylmethylsiloxane (synthesized by hydrolysis of a fluoroalkylmethyldichlorosilane), with ⁇ , ⁇ -dihydroxypolydimethylsiloxane (synthesized by hydrolysis of dimethyldichlorosilane), or chain extension of ⁇ , ⁇ -dihydroxypolyfluoroalkylmethylsiloxane and ⁇ , ⁇ -dihydroxy-polydimethylsiloxane in the presence of e.g., Me 3 SiOH.
  • cyclic organopolysiloxane of formula (c) is a random copolymer or block copolymer, a block copolymer being preferred for this component.
  • Examples of synthesis methods for the preparation of the cyclic organopolysiloxane of formula (c) include the following: equilibrating an ⁇ , ⁇ -dihydroxyfluoroalkylmethylsiloxane/dimethylsiloxane copolymer, (synthesized by the cohydrolysis of a fluoroalkylmethyldichlorosilane with dimethyldichlorosilane), using a conventional basic catalyst, followed by conversion of the equilibrated product to a cyclic product; conventional dehydration polycondensation of an ⁇ , ⁇ -dihydroxy- polyfluoroalkylmethylsiloxane (synthesized by hydrolysis of a fluoroalkylmethyldichlorosilane) with ⁇ , ⁇ -dihydroxypolydimethyl-siloxane (synthesized by hydrolysis of dimethyldichlorosilane) or chain extension.
  • An organic solvent is often used for the synthesis
  • any conventional type of reinforcing silica powder can be used for component (D) of the composition of this invention as a filler.
  • these powders include the following: fumed silica fine made by a dry method, sintered silica powder, precipitated silica powder made by a wet method.
  • Hydrophobic silica powder with surfaces which have been treated with either dimethyldichlorosilane or hexamethyldisilazane also can be used.
  • the specific surface area of this component is equal to 50 m 2 /g or more, preferably 100-400 m 2 /g.
  • the content of this component is 10-100 parts by weight per 100 parts by weight of component (A), preferably 20-50 parts.
  • a curing agent is used as component (E) of this invention for curing the composition.
  • Any conventional type of curing agent used for curing a silicone rubber composition is suitable.
  • curing agents include the following: agents consisting of a combination of either organic peroxide or an organohydrogen polysiloxane containing 2 or more silicon-bonded hydrogen atoms per molecule and a platinum catalyst.
  • organic peroxides include the following: benzoyl peroxide, dicumyl peroxide, ditert-butyl peroxide, tert-butylmonochlorobenzoyl peroxide, and 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane.
  • organohydrogen polysiloxanes include: dimethylsiloxane/methyl hydrogen siloxane copolymers, both ends of which are terminated with trimethylsiloxy groups; methyl hydrogen polysiloxanes, both ends of which are terminated with trimethylsiloxy groups; cyclic methyl hydrogen siloxane.
  • platinum catalysts include: chloroplatinic acid, complexes of chloroplatinic acids and olefin compounds; and complexes of chloroplatinic acid and divinyltetramethyldisiloxane.
  • composition of this invention is prepared by homogeneously mixing all of the above-mentioned components (A)-(E). Any conventional additive used for silicone rubber compositions may also be used in addition to these components.
  • additives examples include diorganopolysiloxanes containing silanol endgroups and having a low polymerization degree.
  • This diorganopolysiloxane is used as a wetting agent for increasing the affinity between component (A) (diorganopolysiloxane) and component (D) (reinforcing silica powder).
  • organic groups contained in a main chain of this additive diorganopolysiloxane include the following: alkyl groups such as methyl groups, ethyl groups, and propyl groups; aryl groups such as phenyl groups; alkenyl groups such as vinyl groups; and 3,3,3-trifluoropropyl groups.
  • a F(CF 2 ) a CH 2 CH 2 group may be included as an organic group to increase compatibility with the organopolysiloxane of component (C).
  • the preferred polymerization degree for the organopolysiloxane additive is 2-100, preferably 2-30.
  • other additives which may be used include: volume-increasing fillers such as finely crushed quartz, diatomaceous earth, calcium carbonate, and aluminosilicate; heat-resistant agents such as iron oxide, cerium oxide, aluminum oxide, zinc oxide, and manganese carbonate; fire-retardant agent; titanium; and carbon black.
  • the composition of this invention contains component (C) which is used as a compatibilizing agent, the compatibility between components (A) and (B) is increased; this results in an improvement in the dispersibility of component (B) in component (A) and the amount of component (B) to be contained in the composition can be increased. Accordingly, a silicone rubber having good physical properties and exhibiting no damage to either the processability or molding properties can be made.
  • a kneader mixer 100 parts of a diorganopolysiloxane containing vinyl groups whose ends had been terminated with dimethylvinylsiloxy groups, having a value of 7,000 for the average polymerization degree, and consisting of 99.5 mol% dimethylsiloxane units and 0.5 mol% methylvinylsiloxane units, 1 part of polytetrafluoroethylene resin powder having an average particle size distribution of 0.2-0.3 ⁇ m (Mitsui Du Pont Fluorochemical K.K., brand: Teflon® 6C-J), 1 part of an organopolysiloxane of the formula F(CF 2 ) 8 C 2 H 4 SiMe 2 O(Me 2 SiO) x' SiMe 2 C 2 H 4 (CF 2 ) 8 F in which x ' is the value required to provide a viscosity of 50 mPa.s (cP), 35 parts of fumed silica
  • the silicone rubber base of Example 1 (100 parts), was homogeneously mixed with the following; methyl- hydrogenpolysiloxane (1 part), both ends of which were terminated with trimethylsiloxy groups, having a 20 mPa.s (cP) viscosity, a complex of chloroplatinic acid and divinyltetramethyldisiloxane (an amount equivalent to 25 ppm platinum weight), and phenylbutanol used as a reaction inhibitor, (0.05 part).
  • a silicone rubber composition was made and press molded at 150°C under 30 kgf/cm 2 for 10 minute to make a 2 mm-thick silicone rubber sheet. The physical properties of the sheet were measured and the results are shown in Table I.
  • a silicone rubber composition was made by the same process used for Example 1 but the organopolysiloxane of formula F(CF 2 ) 8 C 2 H 4 SiMe 2 O(Me 2 SiO) x' SiMe 2 C 2 H 4 (CF 2 ) 8 F was omitted.
  • the resulting silicone rubber composition was molded in the same pressing process used for Example 1 to make a silicone rubber sheet. However, the viscosity of the composition was so high that it was difficult to fill the mold and a satisfactory sheet could not be made.
  • Diorganopolysiloxane (100 parts) whose ends were terminated with dimethylvinylsiloxane groups, and which consisted of dimethylsiloxane units (99.7 mol%) and methylvinylsiloxane units (0.3 mol%), and having a value of 7,000 for the average polymerization degree was placed in a kneader mixer.
  • Dimethylpolysiloxane (8 parts), both ends of which were terminated with dimethylvinylsiloxane groups, and which had an average polymerization degree of 5, was also placed in the kneader mixer.
  • fumed silica 35 parts
  • fumed silica 35 parts
  • polytetrafluoroethylene resin powder (2 parts) having an average particle size distribution of 0.2-0.3 ⁇ m (Mitsui Du Pont Fluorochemical K.K., brand: Teflon® 6C-J) and an organopolysiloxane (0.8 part) of the formula Me 3 SiO(F(CF 2 ) 8 C 2 H 4 SiMeO) y'' (Me 2 SiO) z'' SiMe 3 (ratio of y '': z '' is equal to 1:5) and having a 500 mPa.s (cP) viscosity, was added, then kneaded for 1 hour.
  • a silicone rubber base was made.

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  • Organic Chemistry (AREA)
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Claims (7)

  1. Composition de caoutchouc de silicone comprenant:
    (A) 100 parties en poids d'un organopolysiloxane contenant des groupes vinyles ;
    (B) 0,01 à 50 parties en poids d'une poudre de résine fluorée ;
    (C) 0,01 à 40 parties en poids d'un organopolysiloxane contenant des unités ayant la formule :

            F(CF2)aCH2CH2Si(Me)nO(3-n)/2

    dans laquelle a est un nombre entier d'au moins 4, n est 0, 1 ou 2 et Me indique un radical méthyle ;
    (D) 10 à 100 parties en poids d'une poudre de silice de renforcement ayant une surface spécifique d'au moins 50 m2/g; et
    (E) une quantité suffisante d'un agent de réticulation pour réticuler ladite composition.
  2. Composition selon la revendication 1, dans laquelle la poudre de résine fluorée (B) est du polytétrafluoroéthylène.
  3. Composition selon la revendication 1, dans laquelle ledit organopolysiloxane (A) est choisi dans le groupe constitué d'un diméthylpolysiloxane comportant des groupes diméthylvinylsiloxy terminaux, des copolymères de diméthylsiloxane et de méthylvinylsiloxane comportant des groupes diméthylvinylsiloxy terminaux, des copolymères de diméthylsiloxane et de méthylvinylsiloxane comportant des groupes triméthylsiloxy terminaux et des copolymères de diméthylsiloxane et de méthylvinylsiloxane comportant des groupes diméthylhydroxysiloxy terminaux.
  4. Composition -selon la revendication 3, dans laquelle ledit composé (C) est choisi dans le groupe constitué des organopolysiloxanes représentés par la formule F(CF2)aCH2CH2Si(Me)2O(Me2SiO)xSiMe2CH2CH2(CF2)aF dans laquelle x est un nombre entier ayant une valeur de 0 à 300 ; la formule Me3SiO(F(CF2)aCH2CH2SiMeO)y(Me2SiO)zSiMe3 dans laquelle y et z sont des nombres entiers ayant une valeur d'au moins 1, le rapport y/z est 0,1 à 0,9 et (y + z) est 2 à 1 000 ; et la formule
    Figure imgb0005
     dans laquelle p et q sont des nombres entiers ayant une valeur d'au moins 1 et (p + q) est 3 à 40.
  5. Composition selon la revendication 1, dans laquelle 0,1 à 20 parties en poids dudit composé (B), 0,1 à 10 parties en poids dudit composé (C) et 20 à 50 parties en poids dudit composé (D) sont utilisées pour chaque 100 parties en poids dudit composé (A).
  6. Composition selon la revendication 1, dans laquelle l'agent de réticulation (E) est choisi parmi un peroxyde organique ou un organohydrogénopolysiloxane et un catalyseur au platine.
  7. Article en caoutchouc réticulé fabriqué à partir de la composition de la revendication 3.
EP94105172A 1993-03-31 1994-03-31 Composition de caoutchouc de silicone Expired - Lifetime EP0618271B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP5096594A JPH06287451A (ja) 1993-03-31 1993-03-31 シリコーンゴム組成物
JP96594/93 1993-03-31

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EP0618271A2 EP0618271A2 (fr) 1994-10-05
EP0618271A3 EP0618271A3 (fr) 1995-06-21
EP0618271B1 true EP0618271B1 (fr) 1997-09-17

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EP (1) EP0618271B1 (fr)
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DE (1) DE69405625T2 (fr)

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JPS6036171A (ja) * 1983-08-09 1985-02-25 Toray Silicone Co Ltd 活字部を有するゴム状弾性部材の製造方法
FR2557121B1 (fr) * 1983-12-21 1986-10-10 Rhone Poulenc Spec Chim Compositions elastomeriques organopolysiloxaniques vulcanisables a chaud a caracteristiques physiques ameliorees
US4945125A (en) * 1987-01-05 1990-07-31 Tetratec Corporation Process of producing a fibrillated semi-interpenetrating polymer network of polytetrafluoroethylene and silicone elastomer and shaped products thereof
JPS63297429A (ja) * 1987-05-29 1988-12-05 Asahi Glass Co Ltd 長鎖フルオロアルキル基含有シリコ−ンオイル
US4980443A (en) * 1989-01-12 1990-12-25 Dow Corning Corporation Fluorosilicone compounds and compositions for adhesive release liners
JP3111454B2 (ja) * 1989-09-08 2000-11-20 旭硝子株式会社 グリース基油
US5302632A (en) * 1991-04-22 1994-04-12 Dow Corning Corporation High consistency organosiloxane compositions comprising fluorinated and non-fluorinated polyorganosiloxanes
JPH05301963A (ja) * 1992-04-27 1993-11-16 Toray Dow Corning Silicone Co Ltd フルオロシリコ−ンポリマーおよび硬化性フルオロシリコーンポリマー組成物

Also Published As

Publication number Publication date
EP0618271A3 (fr) 1995-06-21
US5428097A (en) 1995-06-27
DE69405625T2 (de) 1998-02-05
EP0618271A2 (fr) 1994-10-05
DE69405625D1 (de) 1997-10-23
JPH06287451A (ja) 1994-10-11

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